"I drop my trousers and piss on the king!"
Chaotic Stupid is yet another of the "stupid" alignments. Where Lawful Stupid characters adhere to a restrictive code of conduct beyond the point of reason, Chaotic Stupid characters are marked by their refusal to abide by any kind of code whatsoever, even when it would be reasonable to do so. Some Chaotic Stupid characters take this even further, and will actively break whatever the local laws and customs are, because "I'm chaotic, tee hee!" Another common symptom is mistaking "chaotic" for "whatever random action pops into my head", leading to the synonym of randumb. This provides a criterion for distinguishing Chaotic Stupid from Stupid Evil -- a Stupid Evil character will take actions to cause harm, while a Chaotic Stupid character will just act out.
- Kender. They are "Chaotic Stupid: The Species", as they steal anything that isn't nailed down, and then have the temerity to giggle and act cute about it.
- The Xaositects of Planescape are a social faction dedicated to the philosophy that there is no purpose to the multiverse besides pure chaotic whim, so don't make plans and just do whatever the hell you feel like. In other words, a group for whom Chaotic Stupid is basically the explicitly recommended course. Tend to attract hate from DMs only matched by Kender.
- In a rare example of Chaotic Stupid not being a totally bad thing, Chaos and the Orks from Warhammer 40,000 (and the Orcs and Goblins of Warhammer Fantasy Battle) can exhibit some of this when their own chaotic natures cause them to fight among themselves and collapse any army that threatens the status quo.
- Also Deadpool, but he has a good excuse in that he's completely insane. He also subverts this many times.
- Second edition AD&D described Chaotic Neutral exactly like this. Seriously. Third edition had to specifically revoke this description, making it similar to the problem of Stupid Neutral.
- Malkavians in Vampire: The Masquerade are prone to being played like this because every member of the clan is driven irreparably and uniquely insane upon being turned into a vampire. This has led to the term "Fishmalks" in the community, after one particularly infamous Malkavian PC and art where one was kissing a fish.
- Olive Ruskettle, a female halfling thief from the Forgotten Realms. She stole the name of a famous bard so she could try and usurp his reputation, despite the fact she's a rogue and not a bard (and is in fact described as being "too chaotic to become one"!), feels that "any constraints are too many", dislikes and enjoys picking on anyone who holds strong but narrow beliefs and views (Lawful alignment, devout religious or moral codes, etc), with a particular dislike of paladins, and is generally stated as being irrepressible, impetuous, and completely lacking in foresight.
- "Katy t3h PeNgU1N oF d00m", the supposed author of an old (first seen 2006 or so) 4chan copypasta.
- Charlie Kelly from Its Always Sunny in Philadelphia, specifically the episode "The Gang Solves the Gas Crisis". Upon being told that he was the "wild card" of the gang, he uses this role as a justification for increasingly erratic behavior, culminating in him cutting the brakes of the van they were in for no other reason than "Wild Card, bitches!"
How to be Chaotic without being Stupid
As any alignment thread on /tg/ will show you, defining the "Lawful/Chaotic" axis in a way that is totally orthogonal to "Good/Evil" is very tricky. There is also the matter that any sane character will have some internal code of conduct, so it is not possible to define Lawful as "follows some laws, any laws" and Chaotic as "follows no laws whatsoever". One potentially useful interpretation of that axis that can avoid stupidity or strawmen is to think of Lawful as emphasizing working "by-the-book" for the whole (with the nature of that book separating Lawful Good from Lawful Evil), and Chaotic as emphasizing individual freedom to achieve one's own desires (with the nature of those desires separating Chaotic Good from Chaotic Evil). A way to be Chaotic without being Stupid, therefore, is to determine the character's goals, and have them achieve those goals by whatever method they think is best. This might mean following the rules, if playing nice with the Paladin to stay out of jail is a prerequisite for that goal, but if breaking a few laws is what it takes, then so be it.
As far as that lawful neutral (or hopefully not stupid) guy in the party? Remember, you can find something to like about that character too. We're past the days where alignments only hung around with each other. Make a friend. Don't be uptight about chaos. It's not like you're forbidden by a code of conduct to have lawful friends, right?